720 D Simonton St

Key West, FL 33040

$4,990,000
Price
4
Beds
2,441 Sq. Ft.
$2,044 / Sq. Ft.
2,441
Sq. Ft.
$2,044
per Sq. Ft.
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Property Map
720D Simonton Floor Plan

Description

KEY WEST'S UNLIKELY SANCTUARY | DUAL TRANSIENT LICENSES While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE COMPOUND | Built in 2008 on a generous 5,220sf lot, this 2,441sf property features two distinct units,...KEY WEST'S UNLIKELY SANCTUARY | DUAL TRANSIENT LICENSES While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE COMPOUND | Built in 2008 on a generous 5,220sf lot, this 2,441sf property features two distinct units, a front house and back house, connected by a heated pool oasis. Four bedrooms, four full baths, soaring two-story ceilings, and thoughtfully curated interiors showcase warm mid-century touches against clean architectural lines. Wood and tile floors, built-in cabinetry, walk-in closets, and abundant natural light through expansive glass doors create spaces that are both meditative and functional. | THE SANCTUARY | High privacy walls enclose a tranquil pool courtyard with tropical landscaping, outdoor shower, and ample off-street parking. Electric gate entry ensures complete seclusion while downtown's energy pulses just steps away. | THE OPPORTUNITY | Two active transient rental licenses with 1-day minimum stays unlock exceptional income in Key West's most sought-after location. The property's distinctive design aesthetic attracts discerning guests seeking something different, proven by outstanding reviews and strong rental performance. HNC zoning supports flexible commercial use, while X flood zone designation offers insurance advantages. | THE LOCATION | Heart of Old Town, steps from Duval's legendary dining, nightlife, galleries, and waterfront. Close enough to all the action, far enough from the noise. This is investment-grade real estate with soul, where architectural distinction drives premium rates and occupancy.
  1. Listed by The Spottswood Team • Truman & Co. (KW) • 305-587-3407
  2. Listed by Terri Spottswood • Truman & Co. (KW)

Property Details for 720 D Simonton Street

Waterfront
None
Waterfront
No
Zoning
HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Subdivision
Old Town - Unlisted (1.0)
Directions
Simonton St. between Petronia St. & Angela St.
Vehicle Storage
Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 02/12/2026 02:05 PM

Property Details for 720 D Simonton Street

StatusActive
MLS #618363
Days on Market73
Taxes$31,381 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built2008
Lot Size0.12 AC / 5,220 SF
CountyMonroe County
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Location

Listing Courtesy of Truman & Co. (KW)
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Building Information for 720 D Simonton Street

Stories2Year Built2008Building Size-Lot Size0.12 AC / 5,220 SF

Payment Calculator

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$26,832 per month

30 year fixed, 6.11% Interest

Principal and Interest

$24,217

Property Taxes

$2,615

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 720 D Simonton Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 02 - Key West
  • Absolute Longitude: 81.799736
  • Control Depth: 0
  • Listing Board: Key West Association
  • Side: Median
  • KW Neighborhood: Old Town-N of Truman
  • Mile Marker: 1.0
  • Marathon Neighborhood: N/A
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • License Info: # of City License: 2
  • License Info: Transient Rntl Licns: Yes
  • Fee Includes: None
  • Tax Year: 2025
  • Tax Exemptions: None
Property
Lot Information
  • SqFt Remarks: Buyer to verify square footage
  • Add'l Parcel #1: 00015880-000000
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: KW PT LOT 3 SQR 2 TR 4 OR172-109/10 OR190-476/77 OR333-396/97
  • MLS Approved: Y
  • Bank Owned: No
  • SqFt Source: Property Data Card
  • Flood Zone: X FLOOD ZONE
  • Rentals Allowed: Yes
  • Deed Restrictions: Unknown
  • Picture Count: 59
  • Document Count: 2
  • Building Style: Above Flood: Unknown
  • Property Condition: Updated/Remodeled
  • Security: Electric Gate
Utilities
  • Utilities: FKAA, Buyer to Verify, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: Heated: Yes
  • Pool Info: In Ground, Concrete
  • Porch/Balcony: Open Porch/Balcony, Patio
Interior and Exterior Features
Interior Features
  • Floor: Tile, Wood
  • Interior Features: Drapes/Blinds Incl, Window Treatments, Walk-in Closet(s), Storage, Built-in Cabinets, Pantry
  • Appliances: Washer, Wine Cooler, Freezer, Microwave, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Construction: CBS, Combo Construction, Concrete
  • Dockage: None
  • Exterior Features: Detached Guest Qtrs, Water Display, Storage, Privacy Wall/Fence, Outdoor Shower, Lighting
  • Windows/Doors: Glass Doors, Aluminum Windows, Sliding Glass Doors
Room Information
  • Specialty Rooms: Guest/Servant Qtrs: Legal

Property History for 720 D Simonton Street

DateEvent & SourcePriceAppreciation
Jan 12, 2026

Listed (Active)

FKMLS #618363

$4,990,000—
Aug 4, 2022

Sold

FKMLS #602118

$4,700,000—
Aug 4, 2022

Pending

FKMLS #602118

—
Aug 4, 2022

Listed (Active)

FKMLS #602118

$4,699,000—
DateEvent & SourcePrice
01/12/2026

Listed (Active)

FKMLS #618363

$4,990,000
08/04/2022

Sold

FKMLS #602118

$4,700,000
08/04/2022

Pending

FKMLS #602118

—
08/04/2022

Listed (Active)

FKMLS #602118

$4,699,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Schools near 720 D Simonton Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Horace O'bryant School
Public - PK to 8
Key West High School
Public - 9 to 12
Monroe Virtual Instruction Program
Public - K to 12
Monroe Virtual Franchise
Public - 6 to 12
Rating
School
Distance
Horace O'bryant School
PublicPK to 8

Key West High School
Public9 to 12

Monroe Virtual Instruction Program
PublicK to 12

Monroe Virtual Franchise
Public6 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 720 D Simonton Street, Key West, FL 33040

720 D Simonton Street is a single family home for sale in Key West, FL 33040. This property was listed for sale on January 12, 2026 by Truman & Co. (KW), it's currently listed at $4,990,000. It has been on the market for a total of 73 days and was last sold on August 4, 2022. This listing's school district is Monroe. Nearby schools include Horace O'bryant School, Key West High School and Monroe Virtual Instruction Program. 720 D Simonton Street is a 4-bed, 4-bath, 2,441 sqft single family home built in 2008.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Truman & Co. (KW)

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.